US10800862B2 - Amino silane-based compound, method of preparing the same, and modified conjugated diene-based polymer including the compound - Google Patents
Amino silane-based compound, method of preparing the same, and modified conjugated diene-based polymer including the compound Download PDFInfo
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- US10800862B2 US10800862B2 US16/307,213 US201716307213A US10800862B2 US 10800862 B2 US10800862 B2 US 10800862B2 US 201716307213 A US201716307213 A US 201716307213A US 10800862 B2 US10800862 B2 US 10800862B2
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- 229920000642 polymer Polymers 0.000 title claims abstract description 62
- 150000001993 dienes Chemical class 0.000 title claims abstract description 57
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 59
- 125000003827 glycol group Chemical group 0.000 claims abstract description 28
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- 239000000178 monomer Substances 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000654 additive Substances 0.000 claims description 20
- 230000000996 additive effect Effects 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- -1 lithium alkoxide Chemical class 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 150000002902 organometallic compounds Chemical class 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 125000005490 tosylate group Chemical group 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- SRSLCAIQLIWRQP-UHFFFAOYSA-N N,N-bis[2-[2-(2-butoxyethoxy)ethoxy]ethyl]-3-triethoxysilylpropan-1-amine Chemical compound C(CCC)OCCOCCOCCN(CCC[Si](OCC)(OCC)OCC)CCOCCOCCOCCCC SRSLCAIQLIWRQP-UHFFFAOYSA-N 0.000 claims description 4
- SPAXSTHZVHRTJH-UHFFFAOYSA-N N,N-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3-triethoxysilylpropan-1-amine Chemical compound COCCOCCOCCN(CCC[Si](OCC)(OCC)OCC)CCOCCOCCOC SPAXSTHZVHRTJH-UHFFFAOYSA-N 0.000 claims description 4
- DPXHPBHWKAVIAF-UHFFFAOYSA-N N,N-bis[2-[2-[2-(2-butoxyethoxy)ethoxy]ethoxy]ethyl]-3-triethoxysilylpropan-1-amine Chemical compound C(COCCOCCOCCOCCCC)N(CCOCCOCCOCCOCCCC)CCC[Si](OCC)(OCC)OCC DPXHPBHWKAVIAF-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 3
- DUCCVWKPTDSNFX-UHFFFAOYSA-N N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-3-triethoxysilyl-N-(3-triethoxysilylpropyl)propan-1-amine Chemical compound COCCOCCOCCN(CCC[Si](OCC)(OCC)OCC)CCC[Si](OCC)(OCC)OCC DUCCVWKPTDSNFX-UHFFFAOYSA-N 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims description 3
- 239000011147 inorganic material Substances 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 2
- ZWPUOFSQNASCII-UHFFFAOYSA-N 1-(2-ethoxyethoxy)butane Chemical group CCCCOCCOCC ZWPUOFSQNASCII-UHFFFAOYSA-N 0.000 claims description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- CSBDTEMAXHVRBB-UHFFFAOYSA-N 2-ethoxy-n,n-dimethylethanamine Chemical compound CCOCCN(C)C CSBDTEMAXHVRBB-UHFFFAOYSA-N 0.000 claims description 2
- ZATOFRITFRPYBT-UHFFFAOYSA-N C1=CC=C2C([Li])=CC=CC2=C1 Chemical compound C1=CC=C2C([Li])=CC=CC2=C1 ZATOFRITFRPYBT-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
- 229960004132 diethyl ether Drugs 0.000 claims description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 claims description 2
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 2
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 claims description 2
- NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 claims description 2
- XBEREOHJDYAKDA-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].CC[CH2-] XBEREOHJDYAKDA-UHFFFAOYSA-N 0.000 claims description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
- 229920001971 elastomer Polymers 0.000 description 57
- 239000005060 rubber Substances 0.000 description 57
- 0 [7*]O[8*]C Chemical compound [7*]O[8*]C 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- 238000006116 polymerization reaction Methods 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 238000005299 abrasion Methods 0.000 description 17
- 239000000377 silicon dioxide Substances 0.000 description 16
- 229920003048 styrene butadiene rubber Polymers 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 239000000446 fuel Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229920003052 natural elastomer Polymers 0.000 description 9
- 229920001194 natural rubber Polymers 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 238000005292 vacuum distillation Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000020169 heat generation Effects 0.000 description 8
- 239000010734 process oil Substances 0.000 description 8
- 238000004073 vulcanization Methods 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 239000002174 Styrene-butadiene Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000004898 kneading Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 4
- 239000004636 vulcanized rubber Substances 0.000 description 4
- IUDNRKGPFWUYIC-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound COCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 IUDNRKGPFWUYIC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920005549 butyl rubber Polymers 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000006011 modification reaction Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 2
- XCOASYLMDUQBHW-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OC)(OC)OC XCOASYLMDUQBHW-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
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- 230000002787 reinforcement Effects 0.000 description 2
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- QTZWXOWMJMLZIH-UHFFFAOYSA-N 1-[diethoxy(methyl)silyl]-n-[[diethoxy(methyl)silyl]methyl]methanamine Chemical compound CCO[Si](C)(OCC)CNC[Si](C)(OCC)OCC QTZWXOWMJMLZIH-UHFFFAOYSA-N 0.000 description 1
- VDNSZPNSUQRUMS-UHFFFAOYSA-N 1-cyclohexyl-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1C1CCCCC1 VDNSZPNSUQRUMS-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- RRRXUCMQOPNVAT-UHFFFAOYSA-N 1-ethenyl-4-(4-methylphenyl)benzene Chemical compound C1=CC(C)=CC=C1C1=CC=C(C=C)C=C1 RRRXUCMQOPNVAT-UHFFFAOYSA-N 0.000 description 1
- VVTGQMLRTKFKAM-UHFFFAOYSA-N 1-ethenyl-4-propylbenzene Chemical compound CCCC1=CC=C(C=C)C=C1 VVTGQMLRTKFKAM-UHFFFAOYSA-N 0.000 description 1
- OIEANVCCDIRIDJ-UHFFFAOYSA-N 1-ethenyl-5-hexylnaphthalene Chemical compound C1=CC=C2C(CCCCCC)=CC=CC2=C1C=C OIEANVCCDIRIDJ-UHFFFAOYSA-N 0.000 description 1
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- QKJGTZOWMVHEHS-UHFFFAOYSA-N triethoxy-[3-(phenyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSC1=CC=CC=C1 QKJGTZOWMVHEHS-UHFFFAOYSA-N 0.000 description 1
- JSXKIRYGYMKWSK-UHFFFAOYSA-N trimethoxy-[2-(2-trimethoxysilylethyltetrasulfanyl)ethyl]silane Chemical compound CO[Si](OC)(OC)CCSSSSCC[Si](OC)(OC)OC JSXKIRYGYMKWSK-UHFFFAOYSA-N 0.000 description 1
- JTTSZDBCLAKKAY-UHFFFAOYSA-N trimethoxy-[3-(3-trimethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CO[Si](OC)(OC)CCCSSSSCCC[Si](OC)(OC)OC JTTSZDBCLAKKAY-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
- C07F7/0878—Si-C bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/25—Incorporating silicon atoms into the molecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
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- Y02T10/862—
Definitions
- the present invention relates to an amino silane-based compound, and more particularly, to an amino silane-based compound having an excellent interaction with a rubber polymer and an inorganic filler, a method of preparing the same, and a modified conjugated diene-based polymer in which excellent tensile strength, abrasion resistance, low fuel consumption property, and wet road surface resistance as well as high heat generation property are obtained by including a functional group derived from the amino silane-based compound.
- a natural rubber, a polyisoprene rubber, or a polybutadiene rubber is known as a rubber material having a low hysteresis loss, but these rubbers may have low wet road surface resistance.
- a conjugated diene-based polymer or copolymer such as a styrene-butadiene rubber (hereinafter, referred to as “SBR”) or a butadiene rubber (hereinafter, referred to as “BR”), is prepared by emulsion polymerization or solution polymerization to be used as a rubber for a tire.
- the greatest advantage of the solution polymerization in comparison to the emulsion polymerization is that a vinyl structure content and a styrene content, which specify physical properties of the rubber, may be arbitrarily adjusted and its molecular weight and physical properties may be controlled by coupling or modification.
- the SBR prepared by the solution polymerization is widely used as a rubber material for a tire because it is easy to change a structure of the finally prepared SBR or BR, and movement of chain ends may be reduced and a coupling force with a filler, such as silica or carbon black, may be increased by coupling or modification of the chain ends.
- the solution-polymerized SBR is used as the rubber material for a tire
- a glass transition temperature of the rubber is increased by increasing a vinyl content in the SBR
- physical properties, such as running resistance and braking force, required for a tire may not only be controlled, but fuel consumption may also be reduced by appropriately adjusting the glass transition temperature.
- the solution-polymerized SBR is prepared by using an anionic polymerization initiator, and is being used by coupling or modification of chain ends of the formed polymer using various modifiers.
- 4,397,994 discloses a technique in which active anions at chain ends of a polymer, which is obtained by polymerization of styrene-butadiene in a non-polar solvent using alkyllithium as a monofunctional initiator, are bonded by using a binder such as a tin compound.
- Carbon black and silica are being used as a reinforcing filler of a tire's tread, wherein, in a case in which the silica is used as the reinforcing filler, the hysteresis loss may be lowered and the wet road surface resistance may be improved.
- the silica having a hydrophilic surface has a low affinity with the rubber in comparison to the carbon black having a hydrophobic surface, dispersibility may be poor, and, thus, there is a need to use a separate silane coupling agent to improve the dispersibility or provide coupling between the silica and the rubber. Therefore, a method of introducing a functional group having an affinity or reactivity with the silica into the ends of rubber molecules is being performed, but its effect is insufficient.
- the present invention provides an amino silane-based compound having an excellent interaction with a rubber polymer and an inorganic filler, a method of preparing the same, a modified conjugated diene-based polymer, in which excellent tensile strength, abrasion resistance, low fuel consumption property, and wet road surface resistance as well as high heat generation property are obtained by including a functional group derived from the amino silane-based compound, and a method of preparing the modified conjugated diene-based polymer.
- R 1 and R 2 are each independently a hydrocarbon group having 1 to 30 carbon atoms, or a glycol unit represented by
- R 3 is a divalent hydrocarbon group having 1 to 30 carbon atoms
- R 4 , R 5 , R 6 , and R 7 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms
- j and k are each independently 0 or 1
- n is an integer selected from 1 to 10
- R 1 and R 2 are glycol units represented by
- i 1 or 2
- l is 0 or 1
- 3-i-l is 1 or 2 when R 1 is a glycol unit represented by
- i and 1 are each independently 1 or 2, but are not 2 at the same time, and 3-i-l is 0 or 1 when R 2 is a glycol unit represented by and
- i 1 or 2
- l is 0 or 1
- 3-i-l is 0 or 1 when both R 1 and R 2 are glycol units represented by
- a method of preparing an amino silane-based compound which includes reacting a compound represented by Formula 2 with a compound represented by Formula 3 in a polar solvent:
- R 3 is a divalent hydrocarbon group having 1 to 30 carbon atoms
- R 4 , R 5 , R 6 , R 7 , and R 9 are each independently a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 8 is a divalent hydrocarbon group having 1 to 10 carbon atoms
- i is an integer of 1 or 2
- j, k, and m are each independently an integer of 0 or 1
- m is 0 or 1 when i is 1
- m is 0 when i is 2
- n is an integer selected from 1 to 10
- X is a leaving group selected from the group consisting of a mesylate group, a tosylate group, and triflate group.
- a modified conjugated diene-based polymer including the amino silane-based compound-derived function group, and a method of preparing the same.
- a conjugated diene-based polymer is modified with an amino silane-based compound including a hydrophilic glycol unit having a high affinity with an inorganic filler, particularly, a silica-based filler
- an amino silane-based compound including a hydrophilic glycol unit having a high affinity with an inorganic filler, particularly, a silica-based filler since a functional group derived from the amino silane-based compound is included at one end of the polymer, preparation of a modified conjugated diene-based polymer having an excellent interaction with the inorganic filler is possible, and the modified conjugated diene-based polymer thus prepared has excellent tensile strength, abrasion resistance, low fuel consumption property, and wet road surface resistance as well as high heat generation property.
- An amino silane-based compound according to the present invention may be represented by Formula 1 below:
- R 1 and R 2 may each independently be a hydrocarbon group having 1 to 30 carbon atoms, or a glycol unit represented by
- R 3 may be a divalent hydrocarbon group having 1 to 30 carbon atoms
- R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 10 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 10
- R 1 and R 2 may be a glycol unit represented by
- i may be 1 or 2
- l may be 0 or 1
- 3-i-l may be 1 or 2 when R 1 is a glycol unit represented by
- i and 1 may each independently be 1 or 2, but may not be 2 at the same time, and 3-i-l may be 0 or 1 when R 2 is a glycol unit represented by and
- i may be 1 or 2
- l may be 0 or 1
- 3-i-l may be 0 or 1 when both R 1 and R 2 are glycol units represented by
- R 1 and R 2 may each independently be a glycol unit represented by
- R 3 may be an alkylene group having 1 to 10 carbon atoms
- R 4 , R 5 , R 6 , and R 7 may each independently be an alkyl group having 1 to 10 carbon atoms
- R 8 may be an alkylene group having 1 to 5 carbon atoms
- i may be 1 or 2
- j, k, and l may each independently be 0 or 1
- 3-i-l may be 0 or 1
- n may be an integer selected from 2 to 8.
- R 1 and R 2 may each independently be a glycol unit represented by
- R 3 may be an alkylene group having 1 to 5 carbon atoms
- R 4 , R 5 , R 6 , and R 7 may each independently be an alkyl group having 1 to 5 carbon atoms
- R 8 may be an alkylene group having 1 to 5 carbon atoms
- i may be 1 or 2
- j, k, and l may each independently be 0 or 1
- 3-i-l may be 0 or 1
- n may be an integer selected from 3 to 6.
- amino silane-based compound represented by Formula 1 may be a compound represented by Formula 1-1 below.
- R 1 may be a glycol unit represented by
- R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 10 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 10.
- R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to 5 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 5 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 5.
- amino silane-based compound represented by Formula 1 may be a compound represented by Formula 1-2 below.
- R 1 and R 2 may each independently be a glycol unit represented by
- R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 10 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 10.
- R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to 5 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 5 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 5.
- amino silane-based compound represented by Formula 1 may be a compound represented by Formula 1-3 below.
- R 1 may be a glycol unit represented by
- R 2 , R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 10 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 10.
- R 2 , R 4 , R 5 , R 6 , and R 7 may each independently be a monovalent hydrocarbon group having 1 to 5 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 3 carbon atoms
- j and k may each independently be 0 or 1
- n may be an integer selected from 1 to 5.
- the expression “monovalent hydrocarbon group” in the present invention may denote a monovalent atomic group, in which carbon and hydrogen are bonded, such as a monovalent alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkyl group containing at least one unsaturated bond, and aryl group, and the monovalent atomic group may have a linear or branched structure depending on its bonding structure.
- divalent hydrocarbon group in the present invention may denote a divalent atomic group, in which carbon and hydrogen are bonded, such as a divalent alkylene group, alkenylene group, alkynylene group, cycloalkylene group, cycloalkylene group containing at least one unsaturated bond, and arylene group, and the divalent atomic group may have a linear or branched structure depending on its bonding structure.
- the amino silane-based compound represented by Formula 1 may be N,N-bis(3-(triethoxysilyl)propyl)-2,5,8,11,14-pentaoxyhexadecan-16-amine, N,N-bis(3-(diethoxy(methyl)silyl)propyl)-2,5,8,11,14-pentaoxyhexadecan-16-amine, N,N-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)3-(triethoxysilyl)propan-1-amine, N,N-bis(2-(2-(2-butoxyethoxy)ethoxy)ethyl)-3-(triethoxysilyl)propan-1-amine, N-(2-(2-methoxyethoxy)ethoxy)-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine,
- the amino silane-based compound may be a modifier for modifying a conjugated diene-based polymer.
- the amino silane-based compound of the present invention may be prepared by a reaction between an amine-based compound containing at least one alkoxysilyl group and a glycol ether-based compound containing a leaving group and a glycol unit.
- a method of preparing an amino silane-based compound according to the present invention may include a step of reacting a compound represented by the following Formula 2 with a compound represented by the following Formula 3 in a polar solvent:
- R 3 may be a divalent hydrocarbon group having 1 to 30 carbon atoms
- R 4 , R 5 , R 6 , R 7 , and R 9 may each independently be a monovalent hydrocarbon group having 1 to 30 carbon atoms
- R 8 may be a divalent hydrocarbon group having 1 to 10 carbon atoms
- i may be 1 or 2
- j, k, and m may each independently be 0 or 1
- m may be 0 or 1 when i is 1
- m may be 0 when i is 2
- n may be an integer selected from 1 to 10
- X may be a leaving group selected from the group consisting of a mesylate group, a tosylate group, and triflate group.
- R 3 may be an alkylene group having 1 to 10 carbon atoms
- R 4 , R 5 , R 6 , and R 7 may each independently be an alkyl group having 1 to 10 carbon atoms
- R 8 may be an alkylene group having 1 to 5 carbon atoms
- i may be 1 or 2
- j, k, and m may each independently be 0 or 1
- m may be 0 or 1 when i is 1
- m may be 0 when i is 2
- n may be an integer selected from 2 to 8, and
- X may be a mesylate group or a tosylate group.
- R 3 may be an alkylene group having 1 to 5 carbon atoms
- R 4 , R 5 , R 6 , and R 7 may each independently be an alkyl group having 1 to 5 carbon atoms
- R 8 may be an alkylene group having 1 to 5 carbon atoms
- i may be 1 or 2
- j, k, and m may each independently be 0 or 1
- m may be 0 or 1 when i is 1
- m may be 0 when i is 2
- n may be an integer selected from 3 to 6
- X may be a tosylate group.
- the compound represented by Formula 2 may include 3-(triethoxysilyl)propan-1-amine, bis((ethoxy(methyl)(phenyl)silyl)methyl)amine, bis((diethoxy(methyl)silyl)methyl)amine, 3-(diethoxy (methoxy)silyl)-N-(3-diethoxy(methoxy)silyl)propyl)-2-methylpropan-1-amine, 3-(ethoxydimethoxysilyl)-N-(3-(ethoxydimethoxysilyl)propyl)-2-propan-1-amine, 2-methyl-3-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)propan-1-amine, 5-(triethoxysilyl)-N-(3-(triethoxysilyl)propyl)pentan-1-amine, N-(3-(trimethoxysilyl)propyl)butan-1
- the glycol ether-based compound represented by Formula 3 since separation of an atomic group or atomic group ions is easy during a substitution or elimination reaction, the glycol ether-based compound represented by Formula 3 contains a leaving group selected from the group consisting of a mesylate group, a tosylate group, and a triflate group which may be expressed as a good leaving group.
- a leaving group selected from the group consisting of a mesylate group, a tosylate group, and a triflate group which may be expressed as a good leaving group.
- the compound represented by Formula 2 and the compound represented by Formula 3 may be used in stoichiometric amounts, and may specifically be used in a molar ratio (Formula 2:Formula 3) of 1:1 to 1:5, 1:1 to 1:3, or 1:1 to 1:2, and the purity and yield of the amino-silane-based compound are excellent within this range.
- the reaction may be performed at a reaction temperature of 10° C. to 100° C., 20° C. to 90° C., or 50° C. to 80° C., and the purity and yield of the amino-silane-based compound are excellent within this range.
- the reaction may be performed by including a polar additive, and, as a specific example, the polar additive may be an inorganic material or an organic material, wherein the inorganic polar additive, for example, may include a hydride containing an alkali metal or alkaline earth metal; a hydroxide containing an alkali metal or alkaline earth metal; or a carbonate containing an alkali metal or alkaline earth metal, any one thereof or a mixture of two or more thereof may be used, the organic polar additive, for example, may include an amine-based base; or an alkoxy-based base, and any one thereof or a mixture of two or more thereof may be used.
- the polar additive may be triethylamine.
- the polar additive may act as a Lewis base for removing protons remaining in an amine group (Lewis acid) after the reaction, and, in a case in which the reaction is performed by including the polar additive, a reaction rate is improved, and the purity and yield of the amino-silane-based compound are excellent.
- the polar solvent may be a polar aprotic solvent
- specific examples of the polar solvent may be an amide-based solvent; an ether-based solvent; a ketone-based solvent; a sulfoxide-based solvent; a nitrile-based solvent; or an alcohol-based solvent such as isopropyl alcohol (IPA), and any one thereof or a mixture of two or more thereof may be used.
- the polar solvent may be acetonitrile.
- a modified conjugated diene-based polymer according to the present invention may include a conjugated diene-based monomer-derived repeating unit, and may include an amino silane-based compound-derived function group represented by the following Formula 1 at one end.
- the conjugated diene-based monomer-derived repeating unit may denote a repeating unit formed by polymerization of a conjugated diene-based monomer
- the conjugated diene-based monomer for example, may include at least one selected from the group consisting of 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, piperylene, 3-butyl-1,3-octadiene, isoprene, 2-phenyl-1,3-butadiene, and 2-halo-1,3-butadiene (the expression “halo” denotes a halogen atom).
- the modified conjugated diene-based polymer may be a copolymer further including an aromatic vinyl monomer-derived repeating unit in addition to the conjugated diene-based monomer-derived repeating unit.
- the aromatic vinyl monomer-derived repeating unit may denote a repeating unit formed by polymerization of an aromatic vinyl monomer, and the aromatic vinyl monomer, for example, may include at least one selected from the group consisting of styrene, ⁇ -methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-propylstyrene, 1-vinylnaphthalene, 4-cyclohexylstyrene, 4-(p-methylphenyl)styrene, and 1-vinyl-5-hexylnaphthalene.
- the modified conjugated diene-based polymer may include the conjugated diene-based monomer-derived repeating unit in an amount of 50 wt % to 95 wt %, 55 wt % to 90 wt %, or 60 wt % to 90 wt %, and the aromatic vinyl monomer-derived repeating unit in an amount of 5 wt % to 50 wt %, 10 wt % to 45 wt %, or 10 wt % to 40 wt %, and rolling resistance, wet road surface resistance, and abrasion resistance are excellent within this range.
- the copolymer may be a random copolymer, and, in this case, a balance between physical properties is excellent.
- the random copolymer may denote that repeating units constituting the copolymer are disorderly arranged.
- the modified conjugated diene-based polymer according to an embodiment of the present invention may have a number-average molecular weight (Mn) of 10,000 g/mol to 2,000,000 g/mol, 100,000 g/mol to 1,500,000 g/mol, or 200,000 g/mol to 800,000 g/mol, and may have a weight-average molecular weight (Mw) of 10,000 g/mol to 5,000,000 g/mol, 150,000 g/mol to 3,000,000 g/mol, or 300,000 g/mol to 1,500,000 g/mol, and the rolling resistance and wet road surface resistance are excellent within this range.
- the modified conjugated diene-based polymer may have a molecular weight distribution (Mw/Mn) of 1.0 to 5.0, 1.1 to 3.0, or 1.3 to 3.0, and the balance between physical properties is excellent within this range.
- the modified conjugated diene-based polymer may have a Mooney viscosity (MV) at 100° C. of 20 to 180, 40 to 150, 60 to 110, or 80 to 110, and processability and productivity are excellent within this range.
- MV Mooney viscosity
- the modified conjugated diene-based polymer may have a vinyl content of 5 wt % or more, 10 wt % or more, or 10 wt % to 50 wt %, and, since a glass transition temperature may be adjusted to an appropriate range, the rolling resistance, wet road surface resistance, and low fuel consumption property are excellent within this range.
- the vinyl content may denote a content of a 1,2-added conjugated diene-based monomer rather than a 1,4-added conjugated diene-based monomer based on 100 wt % of the conjugated diene-based copolymer composed of a monomer having a vinyl group and an aromatic vinyl-based monomer.
- derived repeating unit and “derived functional group” in the present invention may denote a component or structure generated from a certain material or may denote the material itself.
- a method of preparing a modified conjugated diene-based polymer according to the present invention may include a step (S1) of preparing an active polymer coupled with an organometal by polymerization of a conjugated diene-based monomer, or an aromatic vinyl-based monomer with a conjugated diene-based monomer in a hydrocarbon solvent including an organometallic compound; and a step (S2) of reacting the active polymer with an amino silane-based compound represented by Formula 1 below.
- the hydrocarbon solvent is not particularly limited, but, for example, may be at least one selected from the group consisting of n-pentane, n-hexane, n-heptane, isooctane, cyclohexane, toluene, benzene and xylene.
- the compound represented by Formula 1 may be used in an amount of 0.01 mmol to 10 mmol, 0.05 mmol to 5 mmol, 0.1 mmol to 2 mmol, or 0.1 mmol to 1 mmol based on total 100 g of the monomer.
- the organometallic compound may be used in an amount of 0.01 mmol to 10 mmol, 0.05 mmol to 5 mmol, 0.1 mmol to 2 mmol, or 0.1 mmol to 1 mmol based on total 100 g of the monomer.
- the organometallic compound may include at least one selected from the group consisting of methyllithium, ethyllithium, propyllithium, n-butyllithium, s-butyllithium, t-butyllithium, hexyllithium, n-decyllithium, t-octyllithium, phenyllithium, 1-naphthyllithium, n-eicosyllithium, 4-butylphenyllithium, 4-tolyllithium, cyclohexyllithium, 3,5-di-n-heptylcyclohexyllithium, 4-cyclopentyllithium, naphtylsodium, naphtylpotassium, lithium alkoxide, sodium alkoxide, potassium alkoxide, lithium sulfonate, sodium sulfonate, potassium sulfonate, lithium amide, sodium amide, potassium amide, and lithium
- the polymerization of the step (S1) may be performed by including a polar additive, and the polar additive may be added in an amount of 0.001 g to 50 g, 0.001 g to 10 g, or 0.005 g to 0.1 g based on total 100 g of the monomer.
- the polar additive may be at least one selected from the group consisting of tetrahydrofuran, ditetrahydrofurylpropane, diethylether, cycloamylether, dipropyl ether, ethylene dimethyl ether, diethyl glycol, dimethyl ether, tertiary butoxyethoxyethane, bis(3-dimethylaminoethyl)ether, (dimethylaminoethyl)ethylether, trimethylamine, triethylamine, tripropylamine, and tetramethylethylenediamine, and, for example, may be triethylamine or tetramethylethylenediamine, the polar additive may be the same or different from a polar additive which may be added during the preparation of the amino silane-based compound, and, in a case in which the conjugated diene-based monomers, or the conjugated diene-based monomer and the aromatic vinyl-based monomer are copolymerized
- the polymerization of the step (S1) may be anionic polymerization, and, specifically, may be living anionic polymerization in which an anionic active site at polymerization end is obtained by a growth polymerization reaction by anions.
- the polymerization of the step (S1) may be temperature rise polymerization, isothermal polymerization, or constant temperature polymerization (adiabatic polymerization)
- the constant temperature polymerization may denote a polymerization method including a step of performing polymerization not by randomly applying heat but with its own reaction heat after an organometallic compound is added
- the temperature rise polymerization may denote a polymerization method in which the temperature is increased by randomly applying heat after the organometallic compound is added
- the isothermal polymerization may denote a polymerization method in which the temperature of the polymer is constantly maintained by taking away heat or applying heat after the organometallic compound is added.
- the polymerization of the step (S1) for example, may be performed in a temperature range of ⁇ 20°
- the active polymer prepared in the step (S1) may denote a polymer in which a polymeric anion is combined with an organometallic cation.
- the amino silane-based compound represented by Formula 1 may be used in an amount of 0.01 mol to 10 mol, 0.05 mol to 5 mol, or 0.1 mol to 2 mol with respect to 1 mol of the organometallic compound, and, since the optimal modification reaction may be performed within this range, a conjugated diene-based polymer having a high modification ratio may be obtained.
- the reaction of the step (S2) is a modification reaction for the introduction of a functional group derived from the amino silane-based compound into the active polymer, wherein the reaction may be performed in a temperature range of 0° C. to 90° C. for 1 minute to 5 hours.
- the method of preparing a modified conjugated diene-based polymer may be performed by a batch polymerization method or a continuous polymerization method including one or more reactors.
- the method of preparing a modified conjugated diene-based polymer may further include at least one step of recovering solvent and unreacted monomer and drying, if necessary, after the step (S2).
- a rubber composition including the above-described modified conjugated diene-based polymer.
- the rubber composition may include the modified conjugated diene-based polymer in an amount of 10 wt % or more, 10 wt % to 100 wt %, or 20 wt % to 90 wt %, and mechanical properties, such as tensile strength and abrasion resistance, are excellent and the balance between physical properties is excellent within this range.
- the rubber composition may further include another rubber component, if necessary, in addition to the modified conjugated diene-based polymer, and, in this case, the rubber component may be included in an amount of 90 wt % or less based on a total weight of the rubber composition. Specifically, the other rubber component may be included in an amount of 1 part by weight to 900 parts by weight based on 100 parts by weight of the modified conjugated diene-based polymer.
- the rubber component may be a natural rubber or a synthetic rubber, and specific examples of the rubber component may be a natural rubber (NR) including cis-1,4-polyisoprene; a modified natural rubber, such as an epoxidized natural rubber (ENR), a deproteinized natural rubber (DPNR), and a hydrogenated natural rubber, in which the general natural rubber is modified or purified; and a synthetic rubber such as a styrene-butadiene rubber (SBR), polybutadiene (BR), polyisoprene (IR), a butyl rubber (IIR), an ethylene-propylene copolymer, polyisobutylene-co-isoprene, neoprene, poly(ethylene-co-propylene), poly(styrene-co-butadiene), poly(styrene-co-isoprene), poly(styrene-co-isoprene-co-butadiene), poly(sty
- the rubber composition may include 0.1 part by weight to 200 parts by weight or 10 parts by weight to 120 parts by weight of a filler based on 100 parts by weight of the modified conjugated diene-based polymer of the present invention.
- the filler for example, may be a silica-based filler, specific examples of the silica-based filler may be wet silica (hydrous silicic acid), dry silica (anhydrous silicic acid), calcium silicate, aluminum silicate, or colloidal silica, and the filler may preferably be wet silica in which an effect of improving both fracture characteristics and wet grip is the most significant.
- the rubber composition may further include a carbon black-based filler, if necessary.
- silane coupling agent for the improvement of reinforcement and low heat generation property may be used together.
- the silane coupling agent may be bis(3-triethoxysilylpropyl)tetrasulfide, bis(3-triethoxysilylpropyl)trisulfide, bis(3-triethoxysilylpropyl)disulfide, bis(2-triethoxysilylethyl)tetrasulfide, bis(3-trimethoxysilylpropyl)tetrasulfide, bis(2-trimethoxysilylethyl)tetrasulfide, 3-mercaptopropyl trimethoxysilane, 3-mercaptopropyl triethoxysilane, 2-mercaptoethyl trimethoxysilane, 2-mercaptoethyl triethoxysilane, 3-trimethoxysilyl
- the silane coupling agent may preferably be bis(3-triethoxysilylpropyl)polysulfide or 3-trimethoxysilylpropyl benzothiazyl tetrasulfide.
- the modified conjugated diene-based polymer in which a function group having a high affinity with the silica is introduced into the active site, is used as the rubber component, a mixing amount of the silane coupling agent may be reduced in comparison to a conventional case.
- the silane coupling agent may be used in an amount of 1 part by weight to 20 parts by weight or 5 parts by weight to 15 parts by weight based on 100 parts by weight of the silica. Within this range, the silane coupling agent may prevent gelation of the rubber component while sufficiently having an effect as a coupling agent.
- the rubber composition according to the embodiment of the present invention may be sulfur cross-linkable, and may further include a vulcanizing agent.
- the vulcanizing agent may specifically be sulfur powder, and may be included in an amount of 0.1 part by weight to 10 parts by weight based on 100 parts by weight of the rubber component, and, within this range, the low fuel consumption property is excellent while securing elastic modulus and strength required for the vulcanized rubber composition.
- the rubber composition according to the embodiment of the present invention may further include various additives, such as a vulcanization accelerator, process oil, a plasticizer, an antioxidant, a scorch inhibitor, zinc white, stearic acid, a thermosetting resin, or a thermoplastic resin, used in the general rubber industry, in addition to the above-described components.
- additives such as a vulcanization accelerator, process oil, a plasticizer, an antioxidant, a scorch inhibitor, zinc white, stearic acid, a thermosetting resin, or a thermoplastic resin, used in the general rubber industry, in addition to the above-described components.
- a thiazole-based compound such as 2-mercaptobenzothiazole (M), dibenzothiazyl disulfide (DM), and N-cyclohexylbenzothiazole-2-sulfenamide (CZ), or a guanidine-based compound, such as diphenylguanidine (DPG), may be used as the vulcanization accelerator, and the vulcanization accelerator may be included in an amount of 0.1 part by weight to 5 parts by weight based on 100 parts by weight of the rubber component.
- M 2-mercaptobenzothiazole
- DM dibenzothiazyl disulfide
- CZ N-cyclohexylbenzothiazole-2-sulfenamide
- DPG diphenylguanidine
- the process oil acts as a softener in the rubber composition, wherein examples of the process oil may be a paraffin-based, naphthenic-based, or aromatic-based compound, the aromatic-based process oil may be used in consideration of tensile strength and abrasion resistance, and the naphthenic-based or paraffin-based process oil may be used in consideration of hysteresis loss and low temperature characteristics.
- the process oil may be included in an amount of 100 parts by weight or less based on 100 parts by weight of the rubber component, and, within this range, decreases in tensile strength and low heat generation property (low fuel consumption property) of the vulcanized rubber may be prevented.
- antioxidant may be N-isopropyl-N′-phenyl-p-phenylenediamine, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine, 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline, or a high-temperature condensate of diphenylamine and acetone, and the antioxidant may be used in an amount of 0.1 part by weight to 6 parts by weight based on 100 parts by weight of the rubber component.
- the rubber composition according to the embodiment of the present invention may be obtained by kneading the above mixing formulation using a kneader such as a Banbury mixer, a roll, and an internal mixer, and a rubber composition having excellent abrasion resistance as well as low heat generation property may also be obtained by a vulcanization process after molding.
- a kneader such as a Banbury mixer, a roll, and an internal mixer
- the rubber composition may be suitable for the preparation of each member of a tire, such as a tire's tread, an under tread, a sidewall, a carcass coating rubber, a belt coating rubber, a bead filler, a chafer, or a bead coating rubber, or various industrial rubber products such as an anti-vibration rubber, a belt conveyor, and a hose.
- a tire's tread such as a tire's tread, an under tread, a sidewall, a carcass coating rubber, a belt coating rubber, a bead filler, a chafer, or a bead coating rubber
- various industrial rubber products such as an anti-vibration rubber, a belt conveyor, and a hose.
- the present invention provides a tire prepared by using the rubber composition.
- the tire may include a tire or a tire's tread.
- n-hexane 85 wt % of n-hexane, from which impurities, such as moisture, were removed, and 15 wt % of a monomer mixture (73 wt % of butadiene and 27 wt % of styrene) were continuously added at a total flow rate of 400 g/hr to a raw material input line of a first reactor among three continuous stirred-tank reactors (CSTR).
- CSTR continuous stirred-tank reactors
- n-butyllithium for initiating a reaction was added to the input line, and ditetrahydrofurylpropane (DTP), as a polar additive, was added in a molar ratio of 0.5 to 3 with respect to a molar amount of the n-butyllithium.
- DTP ditetrahydrofurylpropane
- an internal temperature of the reactor was controlled to be in a range of 70° C. to 85° C. and was maintained for 30 minutes to 60 minutes.
- a polymer of the first reactor thus obtained was continuously supplied to the top of a second reactor, and an internal temperature of the reactor was controlled to be in a range of 70° C. to 85° C. and was maintained for 60 minutes so that a polymerization conversion rate was 90%.
- a polymer of the second reactor thus obtained was continuously supplied to the top of a third reactor, the compound represented by Formula 1a, which was prepared in Preparation Example 1, was continuously supplied in a molar amount equivalent to that of the n-butyllithium to perform a modification reaction.
- a solution including 5 wt % to 10 wt % of ethyl alcohol and 25 wt % to 35 wt % of an antioxidant (Wingstay-K) was added to a polymer of the third reactor thus obtained at a rate of 1.005 ml/min to stop the polymerization reaction, and a polymer was obtained.
- the polymer obtained was put in hot water heated by steam and stirred to remove the solvent, the residual solvent and water were removed by roll drying to prepare a modified conjugated diene-based polymer.
- Table 1 The results of the analysis of the modified conjugated diene-based polymer thus prepared are presented in Table 1 below.
- Example 2 was performed in the same manner as in Example 1 except that the compound represented by Formula 1b which was prepared in Preparation Example 2, instead of the compound represented by Formula 1a which was prepared in Preparation Example 1, was added in the same molar amount in Example 1.
- Example 3 was performed in the same manner as in Example 1 except that the compound represented by Formula 1d which was prepared in Preparation Example 4, instead of the compound represented by Formula 1a which was prepared in Preparation Example 1, was added in the same molar amount in Example 1.
- Example 4 was performed in the same manner as in Example 1 except that the compound represented by Formula 1e which was prepared in Preparation Example 5, instead of the compound represented by Formula 1a which was prepared in Preparation Example 1, was added in the same molar amount in Example 1.
- Example 5 was performed in the same manner as in Example 1 except that the compound represented by Formula 1g which was prepared in Preparation Example 7, instead of the compound represented by Formula 1a which was prepared in Preparation Example 1, was added in the same molar amount in Example 1.
- Example 6 was performed in the same manner as in Example 1 except that the compound represented by Formula 1h which was prepared in Preparation Example 8, instead of the compound represented by Formula 1a which was prepared in Preparation Example 1, was added in the same molar amount in Example 1.
- Comparative Example 1 was performed in the same manner as in Example 1 except that the compound represented by Formula 1a, which was prepared in Preparation Example 1, was not added in Example 1.
- a weight-average molecular weight (Mw, ⁇ 10 3 g/mol), a number-average molecular weight (Mn, ⁇ 10 3 g/mol), a molecular weight distribution (MWD), and Mooney viscosity (MV) were respectively measured for the modified or unmodified conjugated diene-based polymers prepared in the examples and comparative example. The results thereof are presented in Table 1 below.
- the weight-average molecular weight (Mw) and the number-average molecular weight (Mn) were measured by gel permeation chromatograph (GPC) analysis, and the molecular weight distribution (MWD, Mw/Mn) was obtained by calculation using each molecular weight measured.
- GPC gel permeation chromatograph
- Mw/Mn molecular weight distribution
- the Mooney viscosity (MV, (ML1+4, @100° C.) MU) was measured with a large rotor at a rotor speed of 2 ⁇ 0.02 rpm at 100° C. using MV-2000 (ALPHA Technologies). After samples used in this case were left standing for 30 minutes or more at room temperature (23 ⁇ 3° C.), 27 ⁇ 3 g of each sample was taken and filled into a die cavity, and the Mooney viscosity was measured for 4 minutes by operating a platen.
- Each of the modified or unmodified styrene-butadiene copolymers of the examples and comparative example was used as a raw material rubber and was mixed under mixing conditions shown in Table 2 below. An amount of each raw material in Table 2 was represented by parts by weight based on 100 parts by weight of the rubber.
- the rubber samples were kneaded through first stage kneading and second stage kneading.
- the raw material rubber styrene-butadiene copolymer
- filler styrene-butadiene copolymer
- organosilane coupling agent styrene-butadiene copolymer
- process oil zinc white
- stearic acid stearic acid
- antioxidant anti-aging agent
- wax wax
- an initial temperature of the mixer was controlled to be 70° C. and, after the completion of the mixing, a formulation obtained at a discharge temperature of 150° C. to 160° C. was formed into a synthetic rubber sheet with a roll mill set at 50° C.
- the primary formulation was cooled to room temperature
- the primary formulation, sulfur, a primary vulcanization accelerator and a secondary vulcanization accelerator were added to the mixer, mixing was performed in a state in which the temperature of the mixer was controlled to be 40° C., and a formulation obtained at a discharge temperature of 110° C. or less was formed into a synthetic rubber sheet with a roll mill set at 50° C. to obtain a secondary formulation.
- a curing process was performed at 160° C. for 20 minutes to 30 minutes to prepare each rubber sample.
- Each specimen was prepared according to the tensile test method of ASTM 412, and tensile strength at break of the specimen and tensile stress at 300% elongation (300% modulus) were measured for tensile properties. Specifically, the tensile properties were measured at a rate of 50 cm/min at room temperature using a tensile testing machine, a Universal Test Machine 4204 (Instron).
- Abrasion resistances of the rubber samples prepared were measured using a DIN abrasion tester in such a manner that, after a load of 10 N was applied to a rotating drum with abrasive paper and each rubber sample was moved in a direction perpendicular to a rotational direction of the drum, an abrasion weight loss was measured.
- a rotational speed of the drum was 40 rpm, and a total movement of the sample at the completion of the test was 40 m. The smaller the weight loss was, the better the abrasion resistance was.
- tan ⁇ was measured in a torsion mode at a frequency of 10 Hz while changing a strain at each measurement temperature ( ⁇ 60° C. to 70° C.) using a dynamic mechanical analyzer (TA Instruments).
- the Payne effect was expressed as the difference between the maximum value and the minimum value at a strain of 0.28% to 40%.
- the higher the tan ⁇ at a low temperature of 0° C. was, the better the wet road surface resistance was, and the lower the tan ⁇ at a high temperature of 60° C. was, the lower the hysteresis loss was and the better the low running resistance (fuel economy) was.
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US20190256617A1 (en) | 2019-08-22 |
CN109415539A (zh) | 2019-03-01 |
CN109415539B (zh) | 2021-04-13 |
JP2019534877A (ja) | 2019-12-05 |
EP3524638A1 (de) | 2019-08-14 |
EP3524638A4 (de) | 2019-08-14 |
KR102123080B1 (ko) | 2020-06-15 |
KR20180038950A (ko) | 2018-04-17 |
JP6803977B2 (ja) | 2020-12-23 |
EP3524638B1 (de) | 2020-06-17 |
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